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Communication | Regular issue | Vol 4, No. 7, 1976, pp.1223-1228
Published online, 1st January, 1970
DOI: 10.3987/R-1976-07-1223
Stevens Rearrangement of Berbine Methiodides by Sodium Bis-(2-methoxyethoxy)aluminium Hydride

Tetsuji Kametani,* Shyh-Pyng Huang, Akira Ujiie, Masataka Ihara, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Stevens rearrangement of several berbine methiodides (1, 2, 6, 9 and 11) to the spirobenzylisoquinolines (3, 7, 10 and 12) and the 8-methylberbines (4, 8 and 13) with sodium bis-(2-methoxyethoxy)aluminium hydride is reported. The stereochemistry at the migrating carbon and the relation between the comformation of the quinolizidinium salts and products are also described.